Provincetown sits at the very tip of Cape Cod, where the peninsula curls back on itself and the Atlantic comes in from three sides. It was the first landing of the Mayflower pilgrims in 1620, before they moved on to Plymouth. Today it is best known as one of America's most welcoming towns for LGBT visitors, a fishing port turned arts colony turned summer resort that manages to be simultaneously commercial and genuinely free-spirited.
Commercial Street runs the length of the town — about three miles of galleries, restaurants, boutiques, and guesthouses wedged between the harbor and the dunes. It is pedestrian-friendly in summer, packed with people, and surprisingly easy to navigate on foot or by bicycle. The fishing fleet still works out of Provincetown Harbor, and the catch shows up daily in the restaurants lining the waterfront.
The beaches here are exceptional. Race Point Beach on the National Seashore is a long, wild stretch facing north into open Atlantic; you can watch the sun set over the water here, which is unusual on the East Coast. The Province Lands Visitor Center sits above the dunes and offers a striking view over the whole upper Cape. Whale-watching trips run regularly from MacMillan Pier, with sightings nearly guaranteed in season. Summer is busy and expensive; the shoulder seasons of May and October are calmer, cheaper, and still beautiful.